((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 906076-66-2
• Molecular Formula: C₂₀H₃₀O₄SSi
• Molecular Weight: 394.607

Synonyms:((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

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Technology Process of ((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane

There total 2 articles about ((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

((1R,2S)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane (906076-60-6) → ((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane (906076-66-2)

Guidance literature:

With ammonium acetate; dihydrogen peroxide; Jacobsen's catalyst; In methanol; dichloromethane; at 0 ℃; for 17h;

DOI:10.1021/ol060530l

Reference yield: 71.0%

((1R,2S)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane (906076-60-6) → ((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane (906076-66-2) + C20H30O4SSi (945931-73-7)

Guidance literature:

With urea hydrogen peroxide adduct; sodium carbonate; trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ja071217x

Reference yield: 92.0%

((1S,2S,3R,7S)-6-Benzenesulfonyl-2-methyl-8-oxa-bicyclo[5.1.0]oct-5-en-3-yloxy)-tert-butyl-dimethyl-silane (906076-66-2) + trimethylaluminum (75-24-1) → C21H34O4SSi (945931-96-4) + C21H34O4SSi (945931-78-2)

Guidance literature:

With methylcopper; In tetrahydrofuran; hexane; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ja9017557

upstream raw materials:

((1R,2S)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

(1S,4R,6R,7S)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-4-(3,5-dimethyl-pyrazol-1-yl)-7-methyl-cyclohept-2-enol

C₂₅H₃₈N₂O₄SSi

(1S,2S,6R,7S)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol

((1R,2S)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane

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